[ CAS No. 56724-03-9 ] {[proInfo.proName]}

Name: 56724-03-9|3-Methoxy-2-methylbenzaldehyde|97%
Brand: Ambeed
SKU: A796164
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Quality Control of [ 56724-03-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 56724-03-9 ]

Product Details of [ 56724-03-9 ]

CAS No. :	56724-03-9	MDL No. :	MFCD11044581
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VUVSSLDCCMJFTM-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	13162663
Synonyms :

Calculated chemistry of [ 56724-03-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.29
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	2.36
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	2.44
Consensus Log Po/w :	1.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.53
Solubility :	0.444 mg/ml ; 0.00295 mol/l
Class :	Soluble
Log S (Ali) :	-2.55
Solubility :	0.421 mg/ml ; 0.0028 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.216 mg/ml ; 0.00144 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 56724-03-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 56724-03-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 56724-03-9 ]
Downstream synthetic route of [ 56724-03-9 ]

[ 56724-03-9 ] Synthesis Path-Upstream 1~1

1
[ 74-88-4 ]
[ 56724-03-9 ]
[ 24973-22-6 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4812 - 4815

[ 56724-03-9 ] Synthesis Path-Downstream 1~88

1
[ 56724-03-9 ]
[ 555-31-7 ]
[ 33797-34-1 ]

Reference： [1]Patent: US2281956,1940,

2
[ 56724-03-9 ]
[ 72623-36-0 ]
[ 72623-30-4 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

3
[ 56724-03-9 ]
[ 72623-36-0 ]
[ 72623-30-4 ]
[ 72623-31-5 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

4
[ 72623-18-8 ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

5
[ 591-31-1 ]
[ 74-88-4 ]
[ 56724-03-9 ]

Yield	Reaction Conditions	Operation in experiment
98%		4.1.1.56 3-Methoxy-2-methylbenzaldehyde 58 N',N',N'-Trimethylethylene diamine (1.84 mL, 14.3 mmol) was dissolved in benzene (25 mL) and cooled to 0 C. n-BuLi (5.5 mL, 13 mmol) was added dropwise, and the reaction mixture was stirred for 10 min at room temperature. The reaction mixture was again cooled to 0 C, and m-anisaldehyde (1.54 mL, 13.3 mmol) was added. The reaction mixture was stirred for 15 min at room temperature and then cooled to 0 C. Phenyllithium (22.0 mL, 40.0 mmol) was added dropwise. The reaction mixture was stirred for 12 h at room temperature. THF (20 mL) was then added, and the reaction mixture was cooled to -78 C. Methyl iodide (5.0 mL, 80 mmol) was added dropwise, and the reaction mixture was stirred for 30 min at room temperature. The reaction mixture was poured into cold 10% HCl (50 mL) and extracted with EtOAc (3 * 30 mL). The combined organic phase was dried over sodium sulfate and evaporated under reduced pressure. The crude reaction product was purified using a pre-packed 50 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 2% A/98% B (1 CV), 2% A/98% B ? 20% A/80% B (10 CV), 20% A/80% B (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] to afford 3-methoxy-2-methylbenzaldehyde (2.01 g, 14.3 mmol, 98%) as a yellow oil. 1H NMR (500 MHz, CDCl3) delta 9.97 (1H, s), 7.10 (1H, d, J = 8 Hz), 6.98 (1H, t, J = 8 Hz), 6.74 (1H, d, J = 8 Hz), 3.54 (3H, s), 2.23 (3H, s). 13C NMR (125 MHz, CDCl3) delta 192.0, 157.8, 134.9, 128.9, 126.3, 122.7, 114.8, 55.3, 10.0.
		To a solution of Nu,Nu,Nu'-trimethylethylenediamine (7.1 ml) in toluene (140ml) was added dropwise at 0C nBuLi 1.6M in hexanes (33ml) under nitrogen. The mixture was stirred at rt for 1 h. 3-methoxybenzaldehyde (6.27ml) was added at 0C and the reaction mixture was stirred at rt for 1 h. Phenyllithium 1.8M in di-N-butylether (86ml) was added at 0C and the reaction mixture was stirred at rt overnight. The mixture was cooled down to -75C and iodomethane (19.2ml) was slowly added. The solution was stirred at rt for 4h. The mixture was diluted in cold 10% aq. HCI and the aq. layer was washed three times with EA. The combined org. layers were washed with sat. aq. NaCI, dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 100g cartridge, solvent A: Heptane , solvent B: EA, gradient in %B: 1 to 7 , flow rate: 40 ml/min) to afford 5.75g of a yellow oil. LC-MS (A): tR = 0.78min; [M+H]+: not visible.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[2]Tetrahedron Letters,2004,vol. 45,p. 1793 - 1796
[3]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179
[4]Journal of Organic Chemistry,1989,vol. 54,p. 3730 - 3732
[5]Patent: WO2016/177690,2016,A1 .Location in patent: Page/Page column 88

6
3-Methoxy-2-methylbenzaldehyde Cyclohexylimine [ No CAS ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2463 - 2467

7
3-Methoxybenzaldehyde 2,4-Dimethylpent-3-ylimine [ No CAS ]
[ 74-88-4 ]
[ 56724-03-9 ]
[ 24973-22-6 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4812 - 4815

8
[ 56724-03-9 ]
[ 679433-31-9 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1793 - 1796

9
[ 56724-03-9 ]
[ 679433-30-8 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1793 - 1796

10
[ 56724-03-9 ]
11-methoxy-5-methyl-12b-(3-methyl-butyl)-12a,12b-dihydro-12H-1,4-dioxa-benzo[a]anthracene-2,6-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1793 - 1796

11
[ 56724-03-9 ]
5-bromo-11-methoxy-12b-(3-methyl-butyl)-12a,12b-dihydro-12H-1,4-dioxa-benzo[a]anthracene-2,6-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1793 - 1796

12
[ 591-31-1 ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2463 - 2467

13
[ 133733-30-9 ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 2463 - 2467

14
[ 72623-17-7 ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

15
[ 57598-32-0 ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

16
[ 56724-03-9 ]
[ 92-52-4 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

17
[ 56724-03-9 ]
[ 72623-32-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

18
[ 56724-03-9 ]
[ 72623-37-1 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

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[ 56724-03-9 ]
[ 72623-38-2 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

20
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[ 72623-40-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

21
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[ 72623-40-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

22
[ 56724-03-9 ]
[ 72623-41-7 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1098 - 1106

23
[ 56724-03-9 ]
[ 42981-94-2 ]

Reference： [1]Patent: US2281956,1940,

24
[ 56724-03-9 ]
4-(3-methoxy-2-methyl-phenyl)-3-(4-methoxy-phenyl)-butan-2-one [ No CAS ]

Reference： [1]Patent: US2281956,1940,

25
[ 56724-03-9 ]
[ 765-30-0 ]
[ 790663-45-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a sol. of compound Cl with its regioisomer (1.64 g; 2.853 mmol; 1 eq.) in CH2Cl2 (32 mL) were added at rt cyclopropyl-(3-methoxy-2-methylbenzyl)amine (prepared by reductive amination from 3-methoxy-2-methylbenzaldehyde, Comins, D. L.; Brown, J. D., J. Org. Chem., 1989, 54, 3730 and cyclopropylamine, 1.64 g, 8.56 mmol), DIPEA (1.95 mL, 11.39 mmol) DMAP (87 mg, 0.71 mmol), HOBt (578 mg, 4.28 mmol), and EDC-HCl (2.19 g, 11.413 mmol). The mixture was stirred at rt for 3 days. CH2Cl2 (50 mL) was added to the reaction mixture, and the sol. was washed with aq. IM HCl (3x). The combined aq. layers were extracted with CH2Cl2 (25 mL). The combined org. extracts were washed with aq. sat. NaHCO3 (25 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2C12/CH3OH 100/3) yielded the title compound (1.45 g, 68%). LC-MS: tR = 1.29 min.

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3689 - 3702
[2]Patent: WO2006/64484,2006,A1 .Location in patent: Page/Page column 36

26
[ 19500-02-8 ]
[ 56724-03-9 ]

Yield	Reaction Conditions	Operation in experiment
		(a) N-Benzoyl-3-(3'-methoxy-2'-methyl-phenyl) methyl ester 3-Methoxy-2-methyl-aniline were converted into 3-methoxy-2-methyl-benzaldehyde by the method of Beech (see Example 7).

Reference： [1]Patent: US4058642,1977,A

27
[ 947616-78-6 ]
[ 56724-03-9 ]
(E)-5-bromo-2-[2-(3-methoxy-2-methylphenyl)-vinyl]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 2h;Heating / reflux;	5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-vinyl]-benzoic acid methyl ester (5); To a stirred mixture of (4-bromo-2-methoxycarbonylbenzyl)-triphenylphosphonium bromide (4) (34.2 g; 60.0 mmol), DBU (1,8-diazabicyclo(5.4.0) undec-5-ene; 20.1 g; 132 mmol), and 3-methoxy-2-methylbenzaldehyde (7.21 g; 48.0 mmol) in acetonitrile were heated at reflux temperature for 2 hours. The mixture was cooled and the solvent was evaporated. The residue was partitioned between water and ethyl acetate and the organic phase was washed with 0.1 N HCl, water, and brine. The solution was dried over MgSO4, filtered, and evaporated. The residue was crystallized from ethyl acetate and hexane to yield compound 5 (14.5 g; 84%).

Reference： [1]Patent: US2007/203116,2007,A1 .Location in patent: Page/Page column 9; 10

28
[ 33797-34-1 ]
[ 56724-03-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 3.5h;	A stirred suspension of pyridinium chlorochromate (19.2 g; 89.2 mmol) in dichloromethane at ambient temperature was treated with a solution of (3-methoxy-2-methylphenyl)methanol (9.05 g; 59.47 mmol) in dichloromethane. The reaction solution immediately turned a greenish-brown color. The reaction was stirred for 3.5 hr, diluted 50% with diethyl ether and decanted. The brown gummy residue was triturated twice more with diethyl ether (40 mL) and the ether extracts were combined and evaporated to yield a yellow oil. The oil was passed through a column of silica gel with an ether/hexane mixture to yield the title product, 8.74 g; 97% yield.
85%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	To a well-stirred pyridinium chlorochromate (PCC) in CH2Cl2 (40 mL) solution, (3-methoxy-2-methylphenyl)methanol (3.22 g, 21.2 mmol) dissolved in CH2Cl2 (25 mL) was slowly added.The reaction mixture was stirred at room temperature for 12 h. The mixture was filtered throughCelite, and the Celite was washed thoroughly with CH2Cl2 (2 x 30 mL). The filtrate wasconcentrated under reduced pressure and purified by flash chromatography using a prepacked100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7% A/ 93% B (3 CV), 7%A/ 93% B ? 60% A/ 40% B (10 CV), 60% A/ 40% B (1 CV); flow rate: 25 mL/min; monitoredat 254 and 280 nm] affording the aldehyde (2.70 g, 18 mmol, 85%) as a colorless oil.

Reference： [1]Patent: US2007/203116,2007,A1 .Location in patent: Page/Page column 8
[2]Organic Letters,2020,vol. 22,p. 2914 - 2919
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 253 - 258
Angew. Chem.,2020,vol. 132,p. 259 - 264,6
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[5]Organic Letters,2018,vol. 20,p. 2534 - 2537

29
[ 75-52-5 ]
[ 56724-03-9 ]
[ 1165923-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; at 100℃; for 1h;	Preparation 9: 2-Methyl-1 -(methyloxy)-3-[(E)-2-nitroethenyl]benzene. To a solution of 2-methyl-3-(methyloxy)benzaldehyde (available from Allichem Product List; 2Og; 133 mmol) in nitromethane (400ml) was added ammonium acetate(6.16g; 80 mmol) and the resulting orange mixture was stirred for 1 h at 1000C then cooled to room temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate (x2) and brine, and the organic layers washed with brine, dried(MgSC>4) and concentrated in vacuo. Trituration with dichloromethane/ ether gave the title compound as a yellow solid (6.6g).1H NMR (CDCI3) delta: 8.35 (d, 1 H), 7.48 (d, 1 H), 7.22 (t, 1 H), 7.11 (d, 1 H), 6.96 (d, 1 H), 3.86 (s, 3H), 2.33 (s, 3H)After evaporation of the mother liquors further product (7.22g) was obtained by trituration with diethyl ether. The mother liquors were again evaporated, and the residue was purified by chromatography, eluting with 5-10% ethyl acetate in cyclohexane, to give further product (3.45g) after trituration with ether.
	With ammonium acetate; at 100℃; for 1h;	Preparation 9: 2-Methyl-1-(methyloxy)-3-[(E)-2-nitroethenyl]benzene. To a solution of 2-methyl-3-(methyloxy)benzaldehyde (available from Allichem Product List; 20.Og; 133 mmol) in nitromethane (400ml) was added ammonium acetate (6.16g; 80.0 mmol) and the resulting orange mixture was stirred for 1 h at1000C then cooled to room temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate (x2) and brine, and the organic layers washed with brine, dried (MgSO4) and concentrated in vacuo. Trituration with dichloromethane/ ether gave the title compound as a yellow solid (6.6Og).1H NMR (CHLOROFORM-d) delta: 8.35 (d, 1 H), 7.48 (d, 1 H), 7.22 (t, 1 H), 7.1 1 (d, 1 H),6.96 (d, 1 H), 3.86 (s, 3H), 2.33 (s, 3H).
975 mg	With ammonium acetate; at 100℃; for 1h;	To a solution of 3-methoxy-2-methylbenzaldehyde (1g) in nitromethane (20ml) was added ammonium acetate (310mg). The reaction mixture was stirred at 100C for 1 h. The solution was evaporated in vacuo and the residue was diluted with EA (50ml). The org. layer was washed twice with sat. aq. NaCI, the combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 50g cartridge, solvent A: heptane, solvent B: EA, gradient in %B: 1 , flow rate: 30ml/min) to afford 975mg of a yellow oil. LC-MS (A): tR = 0.89min; [M+H]+: not visible.

Reference： [1]Patent: WO2009/80724,2009,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2009/80728,2009,A1 .Location in patent: Page/Page column 27-28
[3]Patent: WO2016/177690,2016,A1 .Location in patent: Page/Page column 88

30
[ 56724-03-9 ]
[ 1217171-35-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 20℃;Cooling with ice;	To an ice-cooled and stirred suspension of 3-methoxy-2-methylbenzaldehyde (0.269 g, 1.8 mmol) in ethanol (15 ml) a solution of NaOAcJH2O (1.3 eq) and NH2ORHCl (1.3 eq) in water (5 ml) was added dropwise within 5 minutes. The resulting suspension was stirred at room temperature until the starting material was consumed (monitored by TLC). After evaporation of the ethanol in vacuo, water was added to the residue. Then the precipitated crystals were filtered off. The crude product was purified by column chromatography with a mixture of chloroform: ethyl acetate (95:5) as the eluent.Yield: 0.218 g (74%), white crystals. Mp.: 1100C.1H NMR (CDCl3): 2.29 (s, 3H, Ar-CH3); 3.84 (s, 3H, N-CH3); 6.88 (d, IH, Ar); 7.18 (t, IH, Ar); 7.30 (d ,1H, Ar); 8.42 (s, IH, CH); 8.47 (s, IH, N-OH).Analysis calculated for C9H11NO2 (165.19): C 65.44%, H 6.71%, N 8.48%. Found: C 65.45%, H 6.64%, N 8.45%.

Reference： [1]Patent: WO2010/29379,2010,A1 .Location in patent: Page/Page column 16-17

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[ 56724-03-9 ]
[ 1418126-23-4 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

32
[ 56724-03-9 ]
[ 33797-36-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

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[ 56724-03-9 ]
[ 1261616-79-8 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

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[ 56724-03-9 ]
[ 1418126-55-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

35
[ 56724-03-9 ]
[ 1418126-56-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

36
[ 56724-03-9 ]
[ 1418126-57-4 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

37
[ 56724-03-9 ]
[ 1418126-59-6 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

38
[ 67-66-3 ]
[ 56724-03-9 ]
[ 1418126-54-1 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13173 - 13179

39
[ 56724-03-9 ]
5-(3'-methoxy-2'-methylphenyl)pentanoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

40
[ 56724-03-9 ]
2-methoxy-1-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

41
[ 56724-03-9 ]
2-methoxy-1-methyl-5-(3',4',5'-trimethoxyphenyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

42
[ 56724-03-9 ]
3-methoxy-4-methyl-9-(3',4',5'-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulene [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

43
[ 56724-03-9 ]
[ 17857-14-6 ]
5-(3'-methoxy-2'-methylphenyl)pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		4.1.1.57 5-(3'-Methoxy-2'-methylphenyl)pent-4-enoic acid (3) To dissolved 3-(carboxypropyl)triphenyl phosphonium bromide (6.55 g, 15.3 mmol) in THF was added potassium tert-butoxide (3.30 g, 29.0 mmol), and the reaction mixture was stirred at room temperature for 1 h. <strong>[56724-03-9]<strong>[56724-03-9]3-Methoxy-2-methylbenzaldehyd</strong>e</strong> (2.01 g, 13.4 mmol) dissolved in THF was added to the original reaction mixture, and the reaction mixture was stirred at room temperature for 12 h. The THF was evaporated, and the resulting material was quenched with 2 M HCl (75 mL) and extracted with EtOAc (3 * 100 mL). The combined organic phase was evaporated under reduced pressure and purified by flash chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 12% A/88% B (1 CV), 12% A/88% B ? 75% A/25% B (10 CV), 75% A/25% B (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] to afford carboxylic acid 3 (2.12 g, 9.62 mmol, 69%) as a yellow oil. NMR characterization was performed after the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520

44
[ 55289-06-0 ]
[ 56724-03-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7497 - 7520
[2]Journal of Organic Chemistry,2018,vol. 83,p. 1687 - 1700
[3]Organic Letters,2018,vol. 20,p. 2534 - 2537

45
[ 56724-03-9 ]
[ 1165923-81-8 ]

Reference： [1]Patent: WO2016/177690,2016,A1
[2]Molecules,2018,vol. 23

46
[ 56724-03-9 ]
[ 1165923-83-0 ]

Reference： [1]Patent: WO2016/177690,2016,A1

47
[ 56724-03-9 ]
[ 1165923-84-1 ]

Reference： [1]Patent: WO2016/177690,2016,A1

48
[ 56724-03-9 ]
[ 1165923-86-3 ]

Reference： [1]Patent: WO2016/177690,2016,A1

49
[ 56724-03-9 ]
[ 1165923-89-6 ]

Reference： [1]Patent: WO2016/177690,2016,A1

50
C₁₇H₂₈NO₂⁽¹⁺⁾*CF₃O₃S^(1-) [ No CAS ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1687 - 1700

51
N,N-diisopropyl-3-methoxy-2-methylbenzamide [ No CAS ]
[ 56724-03-9 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1687 - 1700

52
[ 90111-15-2 ]
[ 74-88-4 ]
[ 56724-03-9 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg,0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg,0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 muL, 68 mg,0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 734 - 746

53
[ 56724-03-9 ]
[ 65413-33-4 ]
1-(4-(tert-butyl)styryl)-3-methoxy-2-methylbenzene [ No CAS ]
1-(4-(tert-butyl)styryl)-3-methoxy-2-methylbenzene [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2534 - 2537

54
[ 56724-03-9 ]
3-cyclopropyl-N-(3-methoxy-2-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: US2018/118679,2018,A1

55
[ 56724-03-9 ]
3-isopropyl-N-(3-methoxy-2-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: US2018/118679,2018,A1

56
[ 56724-03-9 ]
C₂₆H₃₁N₃O₄ [ No CAS ]

Reference： [1]Patent: US2018/118679,2018,A1

57
[ 56724-03-9 ]
C₁₈H₂₃NO₃ [ No CAS ]

Reference： [1]Patent: US2018/118679,2018,A1

58
[ 56724-03-9 ]
C₂₆H₃₃N₃O₄ [ No CAS ]

Reference： [1]Patent: US2018/118679,2018,A1

59
[ 56724-03-9 ]
[ 20781-20-8 ]
C₁₈H₂₁NO₃ [ No CAS ]